On one hand, some say it's readily doable (https://www.trulia.com/voices/Financing/How_can_I_mortgage_an_investment_property_that_I_o-248127)But this from elsewhere on the infallible Internet (http://forums.moneysavingexpert.com/showthread.php...

With Finance degree he should be able to make a handsome salary even as an entry level employee, and YES !

It almost feels to me that the handsome rent is really a cover to get a cheap option. 

Not sure whether it's a good sign for my project or not.I realise some of these towns are far out but on the other hand some of the 495 ones are commutable to the 495 tech jobs.

If you have the hustle, And you are making contacts with sellers, buyers, investors ect,  you may not be able to buy or sell that deal personally but maybe represent them and make a handsome commission which you can then use to invest.

I bought 1.15 BTC in December of 2016 and sold it at the end of November 2017 for a handsome profit.

Lol I am a single mother of 2 handsome little boys, wanting more in life for them and myself. 

It likely took a while for your friend to build a business that generated a handsome profit and it should take a while to figure out how to invest the proceeds.I'd recommend discussions with commercial brokers, other investors, and RIAs...and more books, podcasts, blogs, posts, etc. 

Other people call it gap financing, what ever the name you need there cash to finish your propject, and will pay them handsomely. 

I rent no where near the 1% rule and yet I still cash flow nicely and make a handsome ROI.